I am guilty of a great many assumptions. There are a lot of things that I take for granted — the types of things that come naturally to me, the perspective I have on things, the business insights I rely on, the experiences I draw from — are all things that frequently turn out to be a bit more unique to me than I always assume.

One of the biggest assumptions I make is that the only real learning — in both life and business — is attained by doing. And usually doing is a constant experiment. Do, make a mistake, re-do, and repeat as needed.

But what about people who actually do learn in a more academic way? People who want and need to first read, then discuss, then process, then internalize and then try? And is it possible to be successful in life — and especially in your own business — if that’s the process you need to go through to learn?

That’s a perfectly fine solution for a 19-year-old, just getting started, who is still in school. But what about a mid-life professional in a career change, or launching a new venture? What do they do? If you’re trying to get a new business off the ground, you don’t get the luxury of pulling to the side of the road and going back to school for a couple of years.

For some of us, that’s ok. In fact, for some of us, that’s fabulous. But for others, it’s overwhelming, upsetting, frightening and debilitating. What is their solution?

The only thing I can think of is finding a mentor. But how does someone who needs an immersive learning experience find a full-time mentor to come into their new business for 3-6 months, and walk with them as they learn to navigate the treacherous world of a startup? Is it possible? And how does an unfunded startup compensate for that?

I’m genuinely curious and truly want to know how to blend a more traditional academic learning aptitude with the daily chaos of a startup business venture. The two feel mutually exclusive to me, but I feel confident that it can’t be an entirely unique problem, either. Someone somewhere must have solved it. But who? And where are they? And what did they do?

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For any entrepreneur, the value of a mentor can almost never be overstated.  Whether it’s building your business plan, defining your market, figuring out a product strategy, or trying to sell your spouse on the idea that giving up a steady paycheck from someone else is a sane thing to do, a mentor is one of the single most valuable things any entrepreneur can find.  Sometimes they come out of the woodwork when you least expect it; other times, you have to go on an aggressive hunt for the right one.

One of the best places for many new entrepreneurs to start is SCORE. (Disclaimer: WorkingPoint is a SCORE sponsor.) SCORE is an organization comprised of small business owners — some actively running businesses, others retired — who work together to build a community to support other small business owners.  While some parts of the country have locally grown networks to support entrepreneurs, SCORE has more than 350 chapters across the US, dedicated to providing counseling and advising services to small business owners.

This week, on SCORE’s Ask an Expert blog, advisor Steve Bloom posted an article on a recent experience he had working with an entrepreneur whose idea was not something he felt had sufficient market to be a viable business.  In the post, Steve recounts the conflict he felt between wanting to encourage the entrepreneurial spirit and the strong sense that this particular idea had extremely long odds of success.

Ultimately, the real point he endevours to drive home, is that whether or not the idea is successful, the entrepreneur can still learn a tremendous amount from trying to get his venture up and running.  The value of the lessons one can learn through failure is something that every entrepreneur must always remember.  In the blogosphere “failing fast” is a common topic, but in reality, most of us are so terrified to fail that we will often turn ourselves inside out in an effort to avoid that experience.

This is one of the places that a mentor can help: a mentor who has been through the process before can not only offer their insight and perspective to help navigate pitfalls, but they can also help remind you that, even in the event of failure, you still get value out of an experience.

One of the most important exercises one of my earliest mentors walked me through was a process of defining my ‘worst case scenario.’  And, amazingly enough, I quickly realized that once I defined my biggest nightmare, it wasn’t anywhere near as scary as it was when it was a nebulous, ill-defined gray cloud hanging over my head; even better, it became much easier to insulate myself from the worst of the possible ramifications once I was clear about the details.

The flip side of Steve’s lesson is equally important: a mentor does not know everything.  And while it’s always nice to have a mentor who understands both you and your idea, the fact is that everyone has different strengths.  Just because a mentor may not consider your venture to be the world’s greatest idea, doesn’t mean it isn’t worth doing.

Part of the test for a mentor is to give you the best advice and encouragement they can; part of the test for an entrepreneur is to listen, process the information, and then make a final determination based on what you know to be true.  You won’t always agree, but that doesn’t make the advice bad, or the mentor wrong.  And hearing those concerns raised is always important, because it helps a new entrepreneur re-examine assumptions and ideas, to make sure there are no holes that have been over-looked.

So, if you have or are looking to start a business, and you do not already have a mentor, I’d strongly recommend looking for one.  There are plenty of different approaches to try (serial entrepreneur Penelope Trunk isn’t above being slightly annoying to snag the one she wants), but whatever you do, start looking for one — check out a local SCORE chapter, Chamber of Commerce, startup incubator or entrepreneurial Meetup.

Wherever you look, just remember: someone who has done it before, always has insights of value for someone just starting out.  They may not all fit, but there is always the chance for some great gems that can help you side-step a landmine.

This post originally appeared as part of my Entrepreneur Evangelist series on WorkingPoint‘s Small Business Blog.

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Some questions are just a trick. The interview process is full of these: there really is no right or wrong answer. The point is just to read something into which option you pick. My favorite of these is the famous one: “Which is more important to you: being liked or being respected?”

As a boss, project manager and organizational leader, the problem is that this question is a bigger trick question than for the average person. I am someone who is expected to get things done. Now, the reality is, most of those things I do not do myself. I get them done by organizing and mobilizing a team of specialists to execute against a plan of action. So that means that my success is dependent on other people.

One of the first lessons I learned as a 24-year-old project manager was that it does not matter which I prefer. What truly matters is what my team needs. And the real danger to this question is that different people need different things.

I used to have a gentleman on my team who was notoriously prickley. Being friends was not part of his MO when it came to work. He had a job to do, he was there to do it. Fuzzy friendly stuff was of no use to him. What was important for me was to understand that. Who cares if what I want is to be liked? The fact is that trying to get that guy to like me was not what he needed from me. All he cared about was respect — whether he felt respected and whether he respected the people around him. “Like” was not part of his equation, and people who wasted time on it were not ones he respected.

Conversely, I had another person on my team who needed a ‘big sister.’ He needed a boss (to be sure), but he needed one with velvet gloves: someone who could be sensitive to his needs, who could guide and advise him, who could encourage and support him, who could help him make plans to meet goals, etc. Yes, he respected me. But that was only possible because he liked and trusted me first and foremost.

One of the biggest failures I see in leaders is assuming that one-size-fits-all leadership works. It doesn’t. People are not IT systems. You can’t configure them to your convenience, turn them on and then walk away.

If you have people on your staff, they are individuals working for an individual — and you failing to meet their need as a manager is the single biggest cause for their departure. So the best way not to fail, is not to assume that everyone responds to the same carrots the same way. Some really do prefer the stick.

So these days, my answer to the question of whether I think it is more important to be liked or respected is simple: “Who cares what is more important to me? The question that really matters is, ‘What’s more important to my team?’”

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Last week I wrote an opening rant about “strategists.” In the comments that ensued, I am now inspired to clarify what I mean while I continue to write this series. I am not talking about consultants who are hired to help hone and build out a strategic vision for an organization; nor am I talking about internal specialists who are dedicated to researching and advising on strategic direction. What I am talking about are managers or department heads who identify as “strategic visionaries” and who consider the banalities of “management” to be less important than defining an over-arching strategy.

The single biggest issue I find when I come into an organization to help get things back on-track, is that when leaders are entirely pre-occupied with a strategic vision, there is a tendency to ignore employee development and management activities.

The irony, of course, is that a good strategist understands that employees are the key to making their strategic vision come to life. Yet time and time again, I have found that groups with the most strategically-focused leaders are the ones where the employees are the most neglected.

The problem, I believe, is in the misalignment of how a leader identifies — and what they actually like to do — versus what is part of the responsibility of the role. How many people who consider themselves innovators, visionaries and strategists are placed in the role of manager? And, honestly, much about managing people is terribly “innovative”? Very little of it. Managing people is down-n-dirty work.

Someone who manages people has to deal with messy details like:

• team members who don’t get along
• people who are not living up to expectations
• talented people who are bored thanks to being under utilized
• political entanglements with other departments
• hiring freezes that prevent backfilling vacated positions
• low morale among teams
• budgetary constraints that prevent a manager from paying an employee what they are truly worth
• helping form a career development plan so team members don’t stagnate
• being honest with a staff member when there is no future for them with the organization

Face it, none of that is sexy. But someone who can’t or won’t do those things is not someone who should be managing people. And yet it happens all the time: a strategically oriented leader is put in the role of a manager, because leadership likes the idea of having a strong strategic direction developed for the department.

Nothing wrong with that. Of course the best departments are marching towards a strategic vision. But if you don’t take care of your team in the process, who exactly is doing the marching?

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My husband constantly points out how irreverent I am. He does this mostly in a light-hearted, good natured way, but he still definitely finds it frustrating. He will often feel like I am being actively disrespectful to individuals or institutions that deserve my deference.

The fact is that I am not disrespectful at all. What I am is an egalitarian. What that often means is that people who are used to getting a higher degree of respect due to their station in life/work will feel like I am being disrespectful because I do not give them any more respect than I give anyone else.

This is actually a bit of an on-going issue/struggle for me, particularly in business (and precisely why I would never survive in the military): I believe in respecting individuals, not rank or title. I have met VPs and C-level execs who take issue with this; and I constantly find myself working with teams who stare at me in shock when I don’t drop what I’m doing to jump whenever the CEO asks for something.

Politically, this certainly causes a problem. I am constantly shocked to discover that smart people let themselves be put in no-win situations and set up for abject failure simply because, to them, it is better to fail than to push back on someone who outranks them.

My husband would likely note that my aversion to failure above all else has more to do with my ego than with anything else. And he wouldn’t be wrong. That is my biggest driver, and I am not embarrassed to admit that. If I allow myself to be compromised out of the gate, I can’t possibly do anyone else any good.

Part of that means that I must honestly tell someone — no matter what their rank — when what they are requesting is unreasonable, impractical or counter-productive to larger objectives. One of the biggest causes for churn and chaos within an organization is a lack of prioritization: constant shifting of focus, no clear objective and whimsical firefighting exercises are not only bad for productivity, but they are bad for morale, bad for quality delivery, bad for reliability and bad for consistency.

Furthermore, I have found that most true leaders want consistency, reliability and productivity above all else. Often times, as Marshall Goldsmith discusses in his classic article, leaders are not aware that their ad hoc comments and requests are creating chaos. That’s not their goal. They certainly understand there is a heavy price to pay for it. But most people are unwilling to point out that is what they are doing.

A long time ago I made a decision, and it’s one of the things that is at the heart of my ability to be successful: my ability to be good depends on my ability to deliver; and reliable, consistent, high-quality delivery is dependent on insulating a team from as much unnecessary chaos as possible. It became very clear to me very early in my career that some of the most dangerous and inadvertent chaos a team can ever experience comes from a company’s leadership team — and often times, leadership doesn’t even know they are doing it. So the most essential role I can provide to my team is to be the person who pushes back on leadership when their requests are undermining the team’s ability to be successful.

That means I don’t drop everything we are doing when the CEO sneezes. That means that I don’t ignore other commitments to lesser ranked colleagues in favor of the President’s morning hot button issue. That means that a client doesn’t get delayed because a VP wants a color change on a website.

I don’t blow anyone off, and I don’t scoff in their face. I present the facts, make my recommendation and then get their feedback. In almost no case in over a decade of doing this have I had a leader listen to what I had to say and then still insist that their pet project was more important than something else.

If that makes me “irreverent,” then so be it, because what it also makes me is reliable. And a true leader trying to get business done knows that reliable delivery is more important than nearly anything else.

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I’ve had an interesting few weeks. My husband and I have been dealing with a lot of things at home, hence my absence from blogging for much of the past month, and I have started a new project with the New Media (a.k.a. “web”) team at KXAN-TV here in Austin.

Between getting settled into the new project and speaking to old friends at former companies (some of whom are now unemployed, while others only wished they were), I’ve been thinking about a number of things that seem to have dovetailed together in a way I wasn’t expecting.

First and foremost is career management. Long a favorite topic of mine, what I’ve been thinking of recently is how sadly common it is for a boss to be totally useless when it comes to helping their employees with career management plans. More than a few of them don’t think it’s part of their responsibility (which I find inexcusably lazy), but even more of them seem to simply not think of it.

This got me thinking of the series I wrote at Christmas, “A Christmas Card to My Bosses: Thanks to Three Very Wise Men.” While I wrote blog posts on the great lessons I learned from each John, Robert and Dave, the thing that I didn’t state explicitly (but which was implicit) was that each of them cared about and was focused on making sure the people on their staff were getting the career development support, encouragement and pushing that they needed. They were all acutely aware of the role they played in developing their people; they took that responsibility seriously and they executed against that.

I see so many talented people who do not have that. And when they finally have someone actually demonstrate some interest and some focus on helping them define and reach their career objectives, they are often so stunned they can hardly believe it.

Why is it so hard? Most people who have been successful enough to be the boss have accomplished that because they know how to manage their own career, so why is it so hard for them to help give guidance and advice to someone else on how to do the same? It shouldn’t be — and I don’t buy that it usually is. I think the reason most people don’t do it is because they don’t make time to do it.

An important thing to keep in mind: statistically speaking, most people do not leave their job, they leave their boss. So are you doing what you need to do to keep your employees engaged and supported so that they stick around? If not, why not?

So that’s my challenge to bosses everywhere: have you worked with each of your direct reports to make sure you understand their career goals (at least as much as they do)? Have you worked on a plan for them that will help them make progress towards those goals? Are you checking in with them regularly to make sure that they are staying focused on at least some of the accomplishments they need in order to stay on track?

Part of being a leader is helping make sure the people you are leading are getting where they need to go. If you aren’t doing that, then where are you leading them?

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This is something I’ve been thinking about more and more recently. The fact that we started off as a services company is what allowed us to get started and to avoid having to rely on outside funding. But it was transitioning to a product company that allowed us to grow and scale, and to ultimately attract funding. However, the transition from one to the other was brutal. And looking back, I can see a thousand opportunities where we could have done a better job.

When the bubble burst back in 2000 it was because speculation had driven realistic performance expectations, sanity and reason out the window (keep throwing endless piles of money at most people, and eventually most of us will get stupid). The industry itself, as well as those watching and investing in it, had bought into its own hype, and then it was crushed under the weight of it’s own hubris and lunacy. (Not unlike what is currently happening to the financial services industry.) Critical lesson: watch the hype and don’t drink the KoolAid. (A caution I would also issue to the current level of hysteria going on in the social media space.)

What this meant, of course, was that companies that had not yet become profitable or did not yet have a self-sustaining business model were S.O.L. VC money evaporated over night. Gone were the massages and catered lunches and lavish holiday parties. Suddenly we were awash in pay cuts, layoffs and absorbing the workloads of people who’d left because we couldn’t afford to replace them.

We were lucky. At that point, we were still a services company (though we were working on our product; it just wasn’t done yet), and that bought us a little bit of time. Not a lot, but — as it turned out — enough. And we sold our asses off. Everything we did for clients was billable. Everything was custom. Everything was a one-off.

Naturally, this presented problems in the scheme of things, because while this was providing us with live-saving revenue, this was not at all scalable. And our leadership knew it. So we continued to push forward with our plans to transition into being a product-based business that offered additional, ancillary services.

The troubles here were strategy, communications, education and execution. For those of us who were living on the services side, we had a culture that was services-centric — not product-centric, and there is a huge difference. In a services-centric culture, your answer to clients is always “yes.” And clients expect your answer to always be “yes.” It never occurs to either of you that the answer could or should be anything else. There is a culture of expectation that must be transitioned, and it must be done thoughtfully and carefully in order to avoid alienating the very people who are keeping you in business.

Now, to be sure, you aren’t going to have a business if you get in the habit of saying “no” to your customers, but there is a big difference between being an order-taking organization whose response to “Jump!” is always, “How high?” and an organization that provides expertise and consultation to customers, as suppliments to a core product offering. The culture, the relationship, the value brought to the table are all very different. And shifting from one to the other is a significant change that needs to be managed carefully in order to keep both your staff and your clients onboard.

Furthermore, our problem was compounded by the fact that the product team was very insulated from the rest of the business. That include socially. They literally sat in a different building. The two groups barely knew each other, so not only did both sides feel misunderstood and taken for granted, but we did not have the opportunity to really find any solid common ground. The services teams thought the product teams were snobs; and the product teams thought the services teams were cowboys. And we were probably all at least a little bit right. But what we weren’t seeing is that each group had a different mission, and that we were each very much in-line with what we needed to be doing at that time.

What we didn’t do was actively execute against a long-term strategy to bring both teams in-line with each other. To whatever degree that did ultimately happen, it was more by brute force of circumstance than by much in the way of active planning or cultivation. Looking back now, so many of the conflicts, headaches, and missteps are painfully clear. And, since hindsight is 20/20, I see so many opportunities that were missed, that would have made all the difference — both when it came to the internal culture, as well as in our relationships with clients.

Of course, looking back, I also now realize that this was one of the early seeds that sparked my interest in change management. This was a big change that had do-or-die implications for the business. The sense of urgency and relevance needed to be truly understood by the services team to get their buy-in, and it simply wasn’t. Without that comprehension, managing client expectations was an endless series of bungled missteps that were constantly needing to be corrected. The services teams needed a roadmap; and we didn’t even have a compass.

Another reason that I love startups is that, given enough time, I know that I’ll have the opportunity to tackle this type of problem again, and be able to apply some of the hard-won lessons from last time to doing it better.

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People who did not meet me until at or around my 25th birthday would never believe it, but in school, I was the Queen of Slackers. Truly. School was too easy, too routine and I spent too long doing it to be able to breath new life into the experience. I could dodge classes, do my homework at the last minute (assuming I did it at all), skip out on reading assignments and skate through tests in my sleep. As a result, I got very, very lazy. I couldn’t see the point of exerting effort on something, if by doing almost nothing I had nearly as good a result.

And then I got a job — that ultimately turned into a career — at a start-up. Pay dirt!

The transformation that sparked in me is still an endless source of amusement among my friends. It took me a while to realize why, but eventually it was clear: the problem with school is that there was an upper limit on what I was capable of achieving. It was an artificial cap on how well I could be scored. I found that inherently disincentivizing. In business, however, there is no upper limit. You can take something as far or as high as you can push it (given the right environment, of course).

And, even better, in a scrappy, entrepreneurial, risk-taking startup (especially one trying to survive an economic downturn) someone who is hungry, talented, teachable and willing to dive into the deep end of the pool head first has tremendous opportunity for growth. The first three years of my career were the most educational, exciting and energizing time of my life — all of my years of school combined couldn’t compare to those three years. Everything was new, everything was interesting and I never once had the slightest bit of doubt that I could conquer anything that came my way.

Ah, the hubris of youth!

Of course, there were downsides. Like many young people, I didn’t know my limits and was constantly pushing the envelope in ways that I probably shouldn’t have (and in ways that I’ve since learned not to do). Whereas many 26-year-olds may be more inclined to do that with parties, I did it with work. I ended up missing a lot of important events in the lives of friends and family because of that.

I was also still extremely idealistic about a great many things. Instead of The Pragmatic Contextualist, an appropriate blog title would have been something along the lines of The Snarky Idealist or Bring it On and Get Out of the Way! (Which, ironically, is still how some people tend to view me, though I have toned down considerably with age.)

But that idealism was invaluable to me, because it made me fearless: if anything is possible and I’m extremely capable, then what do I have to be afraid of? I don’t tend to be very risk-adverse in general, but I have become more cautious with age (though, not quite enough for either my husband or father’s tastes). Back then, though, it would never occur to me that I wouldn’t figure out a way to succeed at whatever I did — which meant I was a hopeless volunteer junkie.

My biggest rush came from fixing problems, and in a post-bubble burst start-up, there were plenty of things to be fixed. So I had an endless supply of opportunity, and endless confidence in my own success. Happily, I also had bosses who went from having nothing to lose by letting me try, to truly believing in my ability to make a positive difference.

As was inevitable, a few kicks in the teeth later, and I stopped being quite so cocky. The pragmatist in me was ultimately born of those experiences, and the eternal idealist retreated to the back, only to come out for the occasional political event.

One of the biggest, most valuable lessons I learned was how to deal with chaos. More recently in my career, I had a bizarre moment when a senior IT Director — who was easily 25 years older than me — groused that we were working in “the most chaotic environment” he’d ever experienced in his life.

I wanted to laugh and call him a weenie (I restrained myself — though barely). The environment we were working in at the time was easily the least chaotic environment I’d ever experienced, and his inability to roll with the punches made him a particularly weak and frustrating leader in my opinion, because he got frazzled very easily, whined constantly and was tremendously rigid. It never occurred to me until that moment that my ability to handle chaos was all that unique.

Naturally, one of the dangers of getting a bit too used to high volumes of chaos is that you can become a drama junkie. This did happen to me, and it took me a while (and outside circumstances) to curb it. But what I have seen of most drama junkies (and trust me, I wasn’t the only one I knew) is that, the older we get, the less tolerance we have for that same constant fever-pitch of insanity.

This is another reason that I have often recommended aimless twentysomethings seeking career advice to explore startups: because by the time people are settled in their career, married or have kids, startups can be a bit too rough on the lifestyle. So if you’re going to do them, best give them a shot while you’re young, energetic, single and have as few external obligations as possible.

But when I look back on that time now, I am profoundly grateful. I was drinking from a fire hose, and it never occurred to me there was any other way to work. I got to sample a spectrum of potential opportunities and figure out which ones held some appeal, and which ones didn’t. If I had found myself in a more stable, structured environment back then, I can’t imagine where I’d be now, because the lessons I learned there, and the all-you-can-eat-buffet of opportunities that I had available to me at the time are how I found my way into a career.

In the scheme of things, I look back on the most pivotal, impactful decisions of my life and the day I left the famed O’Reilly Publishing — which is where I thought I’d wanted to work for years — and went to MarketLive (at the time it was still called MultimediaLive) was one of them. And since then, I have found myself encouraging twentysomethings who do not know what they want out of a career to look at startups, because as long as they can develop a bit of tolerance for chaos (which I firmly believe everyone should do), they’ll usually find opportunities they never knew existed.

What do you think? Are startups a good or bad place to start out your career?

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I had a couple of discussions this week that got me thinking back to the early days of my career. Aside from leaving me feeling older than I care to think about, it did spark a pleasant memory or two that I’ve been mulling over since.

Specifically, I’ve been thinking about how early career choices can really set the stage for the directions we take in life. As is often the case, many of the largest influences on our lives are not obvious until many years later. And while I am as likely as anyone to take them for granted, every once in a while something will happen to make me stop and consider the series of events that brought me to where I am now, and what the unintended consquences of seemingly small actions or events have ultimately provided.

There were three defining elements of my early career that I have been noodling on, because they had much larger impacts on me than I ever would have predicted at the time:

• Getting your start in a startup. What is the value to launching a career in a startup environment?
• Being in the ‘wild west’ of a new market space. What does it mean to be in a new space?
• Transforming a company from being “a services company” to “a product company.” What are the differences and why are they important?

Undoubtedly, the first two of those are a bit sexier than the third. However, all three ultimately shaped me in ways I never fully realized at the time. The lessons learned were a bit rough sometimes, but when I compare some of my experience to that of my peers, I realize that I had the opportunity to be involved in some things that have served me extremely well and that I wouldn’t trade in for anything.

Over the next couple of days, I’ll cover each of these topics in a separate post (each one is too long to combine them).

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At South by Southwest, Brazen Careerist author and CEO Penelope Trunk was quite emphatic that, when starting a new business, having a geographically distributed team is rarely possible. She said this on her panel, as well as again when we spoke in person. She was a strong advocate of the notion that, for the first handful of employees to get a new business off the ground, having everyone in the same room is invaluable.

Conversely, a dear friend who is in the process of developing a business from a one-man shop to a full-scale product company, disagrees strongly. While he has never been an advocate for ‘butts in chairs’ as an organizing model in general, he definitely doesn’t subscribe to the idea that the people you would pull together to get a business started can’t do what they need to do virtually. If someone is good enough for you to enlist to help get a business off the ground, then they should be talented enough to do what they need to do remotely, while communicating with the rest of the team in an effective manner.

However, he does admit to a single hurdle that will quickly need a solution: team-building — which ultimately leads to organizing models and culture.

In the most immediate term, the easiest way around this is for the people working together to found the company to already know each other. If those in the trenches to get it off the ground have worked together in the past, have long-standing relationships (both personal and professional, ideally), and respect each other’s abilities, then it there is a foundation of mutual trust that helps get the ball rolling.

But there are still obstacles with that, even among people with common work histories and mutual trust.

What is everyone doing?

This is the area where newer organizations, if they implement some basic technology solutions in the beginning, can really set a strong precedent for organizational transparency. Enterprise 2.0 has some great capabilities when it comes to finding ways for people to have a transparent audit-trail of their day, that can be visible to everyone.

What code did your developer fix? What are the status of the bugs? How many phone calls did your salesperson make? What is the state of the new partner contract? Has there been any performance degradation today? Which client just requested a new project? Almost all areas of a business can be supported by tools that have standard out-put capabilities (such as RSS), which can be aggregated centrally so that an entire, geographically distributed team can see what is going on in everyone else’s corner of the business.

For some people this is a bit on the creepy ‘big brother’ side. I’ll concede that I can understand why. But this is where the reason for it is important, and where the cultural element is critical: this is about building a culture of transparency, not a culture of mistrust. The “how” and the “why” make all the difference when it comes to the “what.”

If leadership were excluded from this type of transparent work tracking, then it would be easy to argue ‘big brother.’ But the idea is that this starts with an organization’s leadership. They are leading the way by ensuring that their activities are truly transparent.

So much of the Enterprise 2.0 sector is focused on transforming established businesses into transparent and collaborative environments that we don’t spend a lot of time discussing the first rule of building something new: lay the right foundation to begin with, and you can build whatever you want on top of it.

Penelope Trunk made a great point when we spoke: the technology a business chooses to implement speaks to their culture and their values. She is right. Businesses getting started today have almost no technical or financial excuse for not leveraging some great technical solutions — all of which can help reinforce some essential cultural values — to get work done. Cloud computing and SaaS (often freemium) solutions are too pervasive.

If you want your team to collaborate, set up a wiki. If you want feed everyone’s activities for the day into a centralize spot and can’t afford to buy a solution yet, use Yahoo! Pipes. If you want a centralized dashboard that everyone can access easily, use Google Apps. If you’re totally overwhelmed and have no idea what you need, check out Zoho or one of Mashable’s infamous and extremely helpful lists. There are plenty of solutions, most of them with free (or at least very low cost) options. And if you start off using them from day one, they will become part of everyone’s routine and you can skip the painful change management efforts that come with trying alter everyone’s behavior down the line.

Blowing Off Steam, Celebrating and Bonding

Ultimately, the truly hard part about having a virtual team is that there is a certain degree of bonding that really just requires face-to-face interaction. This is where it is most helpful if your virtual team isn’t so far apart as to preclude semi-regular face-time with each other (i.e. if the team is scattered around the Bay Area, but can meet for long lunches/working sessions every couple of weeks at a centralized location). However, sometimes this simply isn’t possible, and the team is a couple thousand miles away (or more). This is where you have a real challenge.

The strongest bonds I’ve ever forged with co-workers — and the point at which co-workers really started becoming true friends — were always a result of bonding under extremely stressful circumstances. It’s the ‘war buddies’ syndrome. You always learn the most about people when you put them under true pressure. And the bonds that form between people under those conditions are commonly very strong. But more often than not, they are strongest when everyone is in the same room.

So how do you truly build a cohesive, trusting, bonded team when everyone is dialed in on an ooVoo conference call from their home office? Particularly once the company starts growing a bit, and it is no longer 2-4 people who all already know each other, how do you start adding in more of the expertise you need without adversely impacting the group dynamic?

This is an on-going source of debate and speculation. Most of the more robust and well-tested virtual team-building models are based around taking formerly co-located teams and re-distributing them (think IBM giving up office space and sending their employees to work from their home offices). So while a quick Google search on “virtual team building” comes up with a host of plausible hits, in the end, most of them are variations on cheesy in-person team building exercises that I rarely find all that effective.

As VC funding continues to dry up, and small startups are forced to do more bootstrapping, geographically distributed companies are going to become increasingly common simply because office space is too expensive and people can’t afford to pick up and move for a low-paying/high-risk startup role. That is going to force a lot of experimentation in this are, and many of these models will have to be developed.

Of course, odds are that my friend’s model will be a common one: if you are going to roll the dice on a new business, it usually feels like a safer bet doing it with someone you not only know, but someone you know you can work with. So, as with many other things about a small startup, you can get away with certain short-cuts in the early days that you have to keep an eye on, because they rarely scale the way you need them to, and if you aren’t paying attention, they’ll come back and bite you before you know it.

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